Holiday rentals in Highland

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Top-rated holiday rentals in Highland

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Guest favourite

Flat in Chicago

4.91 out of 5 average rating, 169 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

10–17 Aug

₹7,061 per night

Guest favourite

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

2–9 Apr

₹7,035 per night

Guest favourite

Home in Munster

4.97 out of 5 average rating, 34 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

30 minute drive from Chicago's Grant Park. Near Little Calumet and Monon trails. Appeals to nature enthusiasts, cyclists, remote workers and brewery aficionados. This 3 bedroom, 1 bathroom retreat offers comfort and convenience. Full kitchen, private backyard and comfortable living space. 3 casinos, 6 breweries: 3 Floyds, 18th Street, Fuzzyline, Byway, New Oberpfalz & Wildrose within 7 to 20 min drive. Early check-ins offered/subject to availability. Feel free to inquire on availability.

5–12 Apr

₹11,202 per night

Guest favourite

Cottage in Valparaiso

4.88 out of 5 average rating, 496 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking a lake. The lake can be accessed from the back yard. - Pet free - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

26 Sep – 3 Oct

₹10,683 per night

Guest favourite

Home in Lansing

4.84 out of 5 average rating, 64 reviews

The Walter Experience

Come indulge in your private oasis located 35 mins from DT chicago. Ideal for Business Travelers(close to I 90/94), Couples ( Perfect Getaway ) and Small Families or friends( Relax & Replenish). Tour our town or neighboring towns ( indiana state line 2 mins away-Munster/Hammond/ Schererville -Lower taxes,Gas,etc. Local entertainment (shows or other events) Complimentary early check in may be extended. Depending on availability, Home is thoroughly cleaned and sanitized before arrival.

8–15 Oct

₹8,412 per night

Guest favourite

Cottage in Gary

4.96 out of 5 average rating, 113 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

9–16 May

₹10,206 per night

Superhost

Flat in Hammond

4.8 out of 5 average rating, 90 reviews

Plant MOOD FREE parking, washer & dryer!

LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING!!! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more Illinois locations!

16–23 Dec

₹6,419 per night

Guest favourite

Barn in Rensselaer

5.0 out of 5 average rating, 275 reviews

The Loft at Virgie

You don't have to be born in a barn to vacation in one. Trade in the city for millions of stars in the night sky! As you enter thru the French doors you will be greeted by an open concept room decorated with a barn/industrial motif. Knotty pine car-siding and galvanized steel, wood floors along with a reclining leather couch and love seat fill the room A full kitchen with granite counter tops await you. There is plenty of natural lighting for the evenings.

23–30 Jan

₹12,405 per night

Guest favourite

Home in De Motte

4.96 out of 5 average rating, 207 reviews

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

25 Nov – 2 Dec

₹9,060 per night

Guest favourite

Guest suite in Crown Point

4.93 out of 5 average rating, 208 reviews

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

27 Jun – 4 Jul

₹6,524 per night

Superhost

Home in Whiting

4.8 out of 5 average rating, 225 reviews

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer

15–22 Nov

₹7,791 per night

Guest favourite

Cottage in Merrillville

4.89 out of 5 average rating, 184 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.

17–24 Jun

₹10,499 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Highland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Highland's top sights

Cracker Barrel Old Country Store3 locals recommend

Langel's Pizza4 locals recommend

Sip Coffee House and Artisan Cafe3 locals recommend

Other great holiday rentals in Highland

Guest favourite

Home in Munster

5.0 out of 5 average rating, 12 reviews

Cozy Farmhouse in Munster

23–30 May

₹9,463 per night

Guest favourite

Home in Gary

4.97 out of 5 average rating, 38 reviews

Private 5 Star 2 bedroom modern city farmhouse

21–28 Nov

₹10,916 per night

Guest favourite

Home in Munster

4.93 out of 5 average rating, 70 reviews

Cozy three bedroom home in Munster , Indiana.

9–16 Mar

₹14,077 per night

Superhost

Flat in Merrillville

4.87 out of 5 average rating, 94 reviews

Lovely 1 bed room apartment, all to yourself.

6–13 Apr

₹8,776 per night

Superhost

Cabin in Gary

4.83 out of 5 average rating, 24 reviews

Rustic 2 bedroom cozy and quiet!

28 Jun – 5 Jul

₹10,213 per night

Guest favourite

Home in Munster

4.9 out of 5 average rating, 82 reviews

Cozy House with Gazebo

3–10 Jul

₹16,399 per night

Guest favourite

Guest suite in Gary

4.98 out of 5 average rating, 48 reviews

Beachfront- Lake Michigan- 2bd/2bath -Heated Pool

9–16 Feb

₹5,316 per night

Guest favourite

Home in Valparaiso

4.97 out of 5 average rating, 87 reviews

Cozy Luxe Downtown Valparaiso Stay

3–10 Sep

₹11,139 per night

Show all

Quick stats about holiday rentals in Highland

Total rentals
10 properties
Local attractions
Cracker Barrel Old Country Store, Wicker Memorial Park and Strack & Van Til
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
120 reviews
Nightly prices starting at
₹5,003 before taxes and fees

Holiday rentals in Highland

Top-rated holiday rentals in Highland

Flat in Chicago

Farm stay in De Motte

Home in Munster

Cottage in Valparaiso

Home in Lansing

Cottage in Gary

Flat in Hammond

Barn in Rensselaer

Home in De Motte

Guest suite in Crown Point

Home in Whiting

Cottage in Merrillville

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Highland holiday rentals

Stay near Highland's top sights

Other great holiday rentals in Highland

Home in Munster

Home in Gary

Home in Munster

Flat in Merrillville

Cabin in Gary

Home in Munster

Guest suite in Gary

Home in Valparaiso

Quick stats about holiday rentals in Highland

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore